Trip Payne was born in Rock Hill, South Carolina on August 7, 1968. He grew up in nearby Spartanburg before attending Emory University in Atlanta, graduating with a degree in English in 1990.

After graduation, he moved to New York and worked for several puzzle magazines before moving back to Atlanta in 1991 to embark upon a freelance puzzlemaking career, which he has been pursuing ever since. He now lives in West Hollywood, California.

Trip's first nationally published puzzle was an easy 15x15 crossword called "Shining Examples" that appeared in the November 1983 issue of Games Magazine. He later interned at Games during his college summer vacations, and would have gone on to work there full-time after college had the magazine not folded two days before his graduation.

Trip's recent regular assignments have included the "wordoku" puzzle in TV Guide, the Yahoo Daily Puzzle with Hints, crosswords in the Puzzle Social Facebook application, themeless crosswords for the Washington Post Puzzler, and many others . He also occasionally writes puzzles for the New York Times, the Wall Street Journal, and other publications, and often authors a puzzle book or two per year for Puzzlewright Press.

He regularly attends several puzzle events every year, including the MIT Mystery Hunt and the National Puzzlers' League convention. He also occasionally goes to other game-related events such as Scrabble and pinball tournaments.

Trip has had two "fifteen minutes of fame" so far. In 1999, he was the third contestant ever to appear on the U.S. version of Who Wants to Be a Millionaire, and was the first to earn $32,000. In 2006, he was one of the crossword solvers profiled in the documentary Wordplay. He has also appeared more briefly on a number of other TV shows (such as an episode of Nightline about the crossword tournament), and has worked on the game shows Million Dollar Password and Scrabble Showdown.